Reductions de cetones α-cyclopropaniques au moyen de l'hydrure de tributyletain

Chemoselective Reductive Amination of Aldehydes and Ketones by Dibutylchlorotin Hydride-HMPA Complex

“…In particular, the effective amination from amino alcohols was noteworthy since it is difficult to isolate the imines because of their instability. 12 Functionalized aromatic aldehydes, 1c and 1e, gave the corresponding amines, 4m-o, selectively ( Table 3, Entries [13][14][15].…”

“…This fact clearly indicates that the reaction with Bu 2 SnClH-HMPA proceeds via ionic process, because a tin radical has been widely recognized to promote the ring opening of cyclopropanes (Scheme 5). 14 Reductive amination of enones is difficult, and only one example using an aliphatic amine and NaBH(OAc) 3 is known. 4a When Bu 2 SnClH-HMPA was employed in the reaction of enone 6j with 2a, allylic amine 7p was formed in 60% yield (Table 4, Entry 19).…”

Rhodium Porphyrin Catalyzed Regioselective Hydrogenolysis of 1,2-Diarylcyclopropanes with Water as the Hydrogen Source

“…Propylbenzene (2a; 0.002 mmol) was obtained in 2% yield, and cyclopropylbenzene (1a; 0.09 mmol) was recovered in 90% yield using naphthalene as the internal standard. Propylbenzene: t R = 6.74; EIMS m/z (rel %) 120 (25), 91 (100), 78 (6), 65 (12), 39 (5). Cyclopropylbenzene: t R = 10.14; EIMS m/z (rel %) 118 (57), 117 (100), 116 (7), 115 (38), 103 (7), 91 (28), 89 (8), 78 (6), 77 (8), 65 (9), 63 (8), 58 (6), 51 (9), 39 (9).…”

“…Propylbenzene: t R = 6.74; EIMS m/z (rel %) 120 (25), 91 (100), 78 (6), 65 (12), 39 (5). Cyclopropylbenzene: t R = 10.14; EIMS m/z (rel %) 118 (57), 117 (100), 116 (7), 115 (38), 103 (7), 91 (28), 89 (8), 78 (6), 77 (8), 65 (9), 63 (8), 58 (6), 51 (9), 39 (9).…”

Regioselective and Room-Temperature Carbon–Carbon Bond Activation of Cyclopropanes by Rhodium(II) Porphyrin

“…However, cyclopropyl phenyl ketone is reduced thermally by tributyltin hydride to give the cyclopropylcarbinol (Scheme 2, C). 6 Therefore, the chemoselective and regioselective addition of nonpolar reagents to cyclopropane remains to be defined.…”